Hydrochloric Acid → HCID 67083938, compound

Participants

Reaction Conditions

Reaction Steps

A 1 L three-necked flask fitted with a reflux condenser and an addition funnel was charged with a magnetic stir bar, 4-bromo-3-ethoxyaniline hydrochloride (25 g, 100 mmol), and anhydrous toluene (300 mL). The reaction mixture was cooled to 0° C. and 100 mL a 1 M solution of boron trichloride in DCM was added to the reaction dropwise via addition funnel. After the addition of the boron trichloride was complete, acetonitrile (6.56 mL, 125 mmol) was added followed by dropwise addition of 110 mL of a 1M solution of TiCl4 in DCM. The resulting heterogenous reaction mixture was heated to reflux for 16 h before being allowed to cool to rt. The crude reaction mixture was carefully poured over 2 M HCl(aq) (˜250 mL) and the reaction mixture was warmed to 80° C. for 1 h. After cooling to rt the pH of the reaction mixture was adjusted to 6 by the careful addition of 2 N NaOH(aq). The solids were filtered and filtrate was extracted with EtOAc (2×1000 mL). The combined organic extract was dried with MgSO4, filtered, and concentrated in vacuo to yield the crude product as a dark oil. MeOH (˜100 mL) was added to the crude oil and the desired product precipitated and was collected via vacuum filtration using a Buchner funnel to yield 10.9 g (42%) of the title compound as a brown solid. m/z 259.

Provenance & Evidence